Tag: M.W=100-150

Nicolaou, K. C. published the artcileSynthesis and Biological Evaluation of Shishijimicin A-Type Linker-Drugs and Antibody-Drug Conjugates, Name: 2-Methyl-2-sulfanylpropan-1-ol, the publication is Journal of the American Chemical Society (2020), 142(29), 12890-12899, database is CAplus and MEDLINE.

Our previous studies with shishijimicin A resulted in the total synthesis of this scarce marine natural product and a number of its simpler analogs endowed with picomolar potencies against certain cancer cell lines. Herein, we describe the design, synthesis, and biol. evaluation of four linker-drugs, anticipating the construction of antibody-drug conjugates (ADCs) as the ultimate goal of this research program. Using a common payload, the assembly of these linker-drugs utilized different linkers and attachment points, providing opportunities to probe the optimal mol. design of the intended ADCs as targeted cancer therapies. In the course of ADC generation and in vitro evaluation, we identified two linker-drugs with a promising in vitro plasma stability profile and excellent targeted cytotoxicity and specificity. Conjugation of shishijimicin A enediyne payloads through their phenolic moiety represents a novel approach to enediyne ADC creation, while the pharmacol. profiles of at least two of the generated ADCs compare well with the profiles of the corresponding clin. approved ADC Kadcyla.

Journal of the American Chemical Society published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Name: 2-Methyl-2-sulfanylpropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Li, Yingwei published the artcileHydrogen Evolution Electrocatalyst Design: Turning Inert Gold into Active Catalyst by Atomically Precise Nanochemistry, Name: 2-Phenylethanethiol, the publication is Journal of the American Chemical Society (2021), 143(29), 11102-11108, database is CAplus and MEDLINE.

Electrocatalytic hydrogen evolution reaction (HER) holds promise in the renewable clean energy scheme. Crystalline Au and Ag are, however, poor in catalyzing HER, and the ligands on colloidal nanoparticles are generally another disadvantage. Herein, we report a thiolate (SR)-protected Au₃₆Ag₂(SR)₁₈ nanocluster with low coverage of ligands and a core composed of three icosahedral (I_h) units for catalyzing HER efficiently. This trimeric structure, together with the monomeric I_h Au₂₅(SR)₁₈^– and dimeric I_h Au₃₈(SR)₂₄, constitutes a unique series, providing an opportunity for revealing the correlation between the catalytic properties and the catalyst′s structure. The Au₃₆Ag₂(SR)₁₈ surprisingly exhibits high catalytic activity at lower overpotentials for HER due to its low ligand-to-metal ratio, low-coordinated Au atoms and unfilled superat. orbitals. The c.d. of Au₃₆Ag₂(SR)₁₈ at -0.3 V vs RHE is 3.8 and 5.1 times that of Au₂₅(SR)₁₈^– and Au₃₈(SR)₂₄, resp. D. functional theory (DFT) calculations reveal lower hydrogen binding energy and higher electron affinity of Au₃₆Ag₂(SR)₁₈ for an energetically feasible HER pathway. Our findings provide a new strategy for constructing highly active catalysts from inert metals by pursuing atomically precise nanoclusters and controlling their geometrical and electronic structures.

Journal of the American Chemical Society published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Name: 2-Phenylethanethiol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tang, Ri-Yuan published the artcileConformation-induced remote meta-C-H activation of amines, Product Details of C7H9NO, the publication is Nature (London, United Kingdom) (2014), 507(7491), 215-220, database is CAplus and MEDLINE.

Achieving site selectivity in carbon-hydrogen (C-H) functionalization reactions is a long-standing challenge in organic chem. The small differences in intrinsic reactivity of C-H bonds in any given organic mol. can lead to the activation of undesired C-H bonds by a non-selective catalyst. One solution to this problem is to distinguish C-H bonds on the basis of their location in the mol. relative to a specific functional group. In this context, the activation of C-H bonds five or six bonds away from a functional group by cyclometallation has been extensively studied. However, the directed activation of C-H bonds that are distal to (more than six bonds away) functional groups has remained challenging, especially when the target C-H bond is geometrically inaccessible to directed metalation owing to the ring strain encountered in cyclometallation. Here we report a recyclable template that directs the olefination and acetoxylation of distal meta-C-H bonds – as far as 11 bonds away – of anilines and benzylic amines. This template is able to direct the meta-selective C-H functionalization of bicyclic heterocycles via a highly strained, tricyclic-cyclophane-like palladated intermediate. X-ray and NMR studies reveal that the conformational biases induced by a single fluorine substitution in the template can be enhanced by using a ligand to switch from ortho- to meta-selectivity.

Nature (London, United Kingdom) published new progress about 14703-69-6. 14703-69-6 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Phenol, name is 3-(Methylamino)phenol, and the molecular formula is C6H12Br2, Product Details of C7H9NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yuan, Shiyu published the artcileMeasurement of non-hindered and hindered phenolic species in aviation fuels via tandem-SPE with comprehensive GC x GC-MS/FID, Application of 4-Propylphenol, the publication is Fuel (2021), 119561, database is CAplus.

Phenolic species have a great impact on the thermal oxidation stability of aviation fuels. However, it is difficult to measure phenolic complex composition and trace content. In this paper, a novel method based on tandem-solid phase extraction (SPE) with comprehensive two-dimensional gas chromatog. (GC x GC)-mass spectrometry (MS) and flame ionization detector (FID) was proposed for measurement of phenolic species in aviation fuels. The tandem of normal phase SPE and anion exchange SPE was employed to extract non-hindered and hindered phenolic species resp. from aviation fuels, and comprehensive GC x GC-MS/FID was used to identify and quantify individual phenolic species with few co-elution. Ninety-eight kinds of phenolic species were identified manually in aviation fuels according to the characteristic m/z and phenolic distribution regular in the 2D chromatogram. Quant. accuracy for phenolic species was verified as their recoveries were satisfactory, especially hindered phenols (BHT), which were totally deprotonated by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Each phenolic species was individually quantified using calibration curve library. Moreover, this work analyzed the adsorption characteristics of phenolic isomers in tandem-SPE procedure and the variation of the contents of phenolic and other oxygenated species after thermal stress. This is an accurate and complete method for measurement of non-hindered and hindered phenolic species in aviation fuels, which is of great significance to establish and improve the kinetic model of thermal oxidation deposition.

Fuel published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C13H14N2O, Application of 4-Propylphenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Cheng, Can published the artcileThe absorption of SO₂ by morpholine cyclic amines with sulfolane as the solvent for flue gas, Formula: C6H13NO2, the publication is Journal of Hazardous Materials (2021), 124462, database is CAplus and MEDLINE.

The absorption properties of N-(2-hydroxyethyl) morpholine (HEM), morpholine (MP) and N-(2-aminoethyl) morpholine (AEM) for SO₂ were studied using sulfolane (SUL) as solvent in this work. Among these solvent combinations, HEM/SUL shows the best cyclic absorption performance, and the capacity of HEM-SUL-40 (40 wt% of HEM and 60 wt% of SUL) to absorb 8580 mg/m³ SO₂ (the remainder is N₂) is 192.18 mg/g at 293.15 K. The absorption capacity of the second cycle is 97.5% of the first absorption cycle, which is higher than 70% of the Cansolv amine solution in a com. application with similar exptl. conditions. However, MP/SUL is difficult to desorb at high temperature, and the absorption capacity of AEM/SUL is much lower than HEM/SUL and MP/SUL. According to the FTIR, ¹H NMR and ¹³C NMR, all three cyclic amines have charge transfer effects with SO₂. The structure of HEM/SUL can be recovered after heating, but MP cannot be recovered. Δ_rG_m° in the reaction against HEM with SO₂ increases significantly with increasing temperature The Δ_rG_m° of HEM-SO₂ and MP-SO₂ at 353.15 K is -12.56 kJ/mol and -16.29 kJ/mol, resp., which further explains the easy desorption of HEM-SO₂ and the difficult desorption of MP-SO₂ at high temperaturesulfur dioxide morpholine cyclic amine sulfolane solvent flue gas.

Journal of Hazardous Materials published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, Formula: C6H13NO2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tian, Wei published the artcileNovel Anthraquinone Compounds Induce Cancer Cell Death through Paraptosis, Synthetic Route of 622-40-2, the publication is ACS Medicinal Chemistry Letters (2019), 10(5), 732-736, database is CAplus and MEDLINE.

Novel anthraquinone compounds that induce ER stress and paraptosis-like cell death were designed and synthesized. Compound I is the first organic micromol. to kill tumor cells by only paraptosis, and its mechanism of action has been further explored. Paraptosis does not appear to involve either phosphatidylserine translocation associated with apoptosis or cell cycle arrest. The bisbenzyloxy and N-(2-hydroxyethyl)formamide structures may be two critical pharmacophores for paraptosis. Bisbenzyloxy can induce ER stress, and the N-(2-hydroxyethyl)formamide structure can increase the ratio of LC3II/I and cytoplasmic vacuolization and facilitates paraptosis. Some antitumor drugs fail to eradicate malignant cell lines with impaired apoptotic pathways; paraptosis may be a route to kill such cells and provides a new potential strategy for cancer chemotherapy.

ACS Medicinal Chemistry Letters published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C14H14, Synthetic Route of 622-40-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Guo, Zhiruo published the artcileSize effect of Ru particles on the self-reforming-driven hydrogenolysis of a lignin model compound, Recommanded Product: 4-Propylphenol, the publication is Catalysis Science & Technology (2022), 12(16), 5143-5151, database is CAplus.

Particle size always has a great influence on catalytic performance. In this study, we investigated the size effect of Ru colloids on the self-reforming-driven hydrogenolysis of a lignin model compound by taking 4-(3-hydroxypropyl)-2-methoxyphenol (PG-OH) as the substrate and NiAl₂O₄ spinel as the support. This reaction provides a strategy to produce alkylphenols from lignin without the consumption of exogenous hydrogen. Three catalysts with different Ru particle sizes (Ru^1.5, Ru^2.6, and Ru^3.3) were prepared, and the catalytic results showed that the reaction activity presented a volcanic curve with the increase in the Ru particle sizes, in which Ru^2.6/NiAl₂O₄ possessed the best performance. Reaction pathway studies showed two different reaction routes over small (Ru^1.5 and Ru^2.6) and large (Ru^3.3) Ru particles. The reforming-driven hydrogenolysis of the methoxy group dominated over small Ru particles, with 4-ethylphenol (4-EP) as the main product; while the hydrogenation of hydroxypropyl and hydrolysis of the methoxy group dominated over the larger particles, with 4-propylcatechin (4-PC) as the main product. Comprehensive investigations indicates the difference in catalytic performance came from the interaction between Ru colloids and the NiAl₂O₄ spinel support, which led to different Ru^δ+/Ru⁰ ratios and finally changed the reaction routes or reaction rate in these three catalysts. This study proves that the particle size really affects catalytic reactions, and indeed, the self-reforming-driven hydrogenolysis of lignin (the model compound) to alkylphenols is structure-sensitive.

Catalysis Science & Technology published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, Recommanded Product: 4-Propylphenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Supranovich, Vyacheslav I. published the artcileGeneration of Alkyl Radicals from Thiols via Zinc Thiolates: Application for the Synthesis of gem-Difluorostyrenes, Synthetic Route of 4410-99-5, the publication is Advanced Synthesis & Catalysis (2021), 363(11), 2888-2892, database is CAplus.

Reaction of thiols with α-(trifluoromethyl)styrenes under photocatalytic conditions led to desulfurative allylic fluorine substitution was described. The reaction was performed by treatment of thiols with benzyl zinc chloride to generate zinc thiolates followed by visible light induced desulfurization by means of triphenylphosphine. Radicals formed after the C-S bond cleavage react with the double bond afforded gem-difluorostyrenes.

Advanced Synthesis & Catalysis published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C10H18O4, Synthetic Route of 4410-99-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lee, Yu Ra published the artcileAlterations in pattern baldness according to sex: hair metabolomics approach, Application of 4-Propylphenol, the publication is Metabolites (2021), 11(3), 178, database is CAplus and MEDLINE.

Pattern baldness has been associated with the male hormone, dihydrotestosterone. In this study, we tried to determine how the overall metabolic pathways of pattern baldness differ in patients and in normal controls. Our study aimed to identify alterations in hair metabolomic profiles in order to identify possible markers of pattern baldness according to sex. Untargeted metabolomics profiling in pattern baldness patients and control subjects was conducted using ultra-performance liquid chromatog.-mass spectrometry. To identify significantly altered metabolic pathways, partial least squares discriminant anal. was performed. Our anal. indicated differences in steroid biosynthesis pathway in both males and females. However, there was a remarkable difference in the androgen metabolic pathway in males, and the estrogen metabolic and arachidonic acid pathways in females. For the first time, we were able to confirm the metabolic pathway in pattern baldness patients using hair samples. Our finding improves understanding of pattern baldness and highlights the need to link pattern baldness and sex-related differences.

Metabolites published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, Application of 4-Propylphenol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yu, Xiaowang published the artcilePolycondensation in confined nanopores toward the selective formation of narrowly dispersed linear polyesters, Related Products of alcohols-buliding-blocks, the publication is Polymer Chemistry (2022), 13(28), 4136-4143, database is CAplus.

The synthesis of linear polymers with both ends conserved is severely impeded due to the inevitable macrocyclization in step-growth polymerization (SGP). Indeed, macrocyclic polymers are considered as the ultimate destination of polycondensations for AB or A₂ + B₂ monomer combinations. Here, we present a new strategy to limit the macrocyclization process towards the selective formation of linear polyesters in the polycondensations of ω-hydroxyaliph. acid and the combinations of dicarboxylic acids and diols. By embedding the catalyst (sulfonic acid) in dendritic mesoporous silica nanoparticles (DMSNs), the polyesterifications were ushered to exclusively take place in the confined nanopores of DMSNs. The distribution of the α,ω-ends in different positions in the bundle of polyesters limited the end-to-end cyclization, leading to the selective chain extension especially in the high mol. weight region. NMR, GPC and MALDI-TOF results show that while the polyesters obtained in homogeneous polycondensation or with a nonporous heterogeneous catalyst were mainly with cyclic structures, the selective formation of linear polyesters was found in the confined nanopores of DMSNs. This finding contradicts the general sense that confined geometries are in favor of macrocyclization and provides a new understanding to manipulate the polymerization process towards the control of cyclic and linear topologies.

Polymer Chemistry published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C6H13NO2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts